How to Keep Online Dating Interesting

A few months back, I was starting to get bored with my online dating profile. The steady stream of nearly identical conversations was slowly but surely wearing out my desire to meet anyone new. Maybe ever. At one point, I was talking to three graduate students whose names started with T, and I couldn’t even begin to tell the difference between them.

So I decided to clear out my inbox by arranging a three-day dating marathon with T1, T2, and T3 as I affectionately called them in my mind. It actually worked out nicely. I could finally stop breezing through flirtatious conversations and figure out which guy stood out from the crowd. His name was Tom.

If you’re feeling like you’re getting into an online dating rut or find the whole experience kind of lame, you’ve come to the right place. There are things you can do on your end to make swiping, chatting, and dating more interesting from start to finish. We’ve come up with several tricks, tips, and ideas to inject some fun into online dating and get better results at the same time. Off we go!

1. Join a New Dating Website — Or Several!

Sometimes being on the same dating site for too long can get you hankering for a change of pace. Maybe you’re starting to see the same suggested matches over and over. Maybe you don’t like the profile setup. Maybe your membership has simply run its course. Joining a new dating site, or two, or three, could be just the change of scenery you need to get your second wind and meet more local singles.

If you haven’t tried Match.com yet, we highly recommend creating a membership for free and connecting with a more steadfast and relationship-minded crowd of singles. The site has connected more relationships and marriages than any other dating sites, so it’s definitely got a lot going on.

Joining a new dating site is like moving to a new town but with less packing, stress, and cardboard boxes. All at once, you’re in an exciting environment surrounded by new people, and you have a whole slew of fresh opportunities to connect with your new neighbors/online daters.

2. Ask Your Crush Thought-Provoking & Off-the-Wall Questions

This is pretty basic, but it’s important to highlight for you bored online daters out there. If you like someone, ask them a question. Any question that comes to mind. What was your favorite movie as a kid? Have you ever traveled outside the country? How many licks does it take to get to the tootsie-roll center of a tootsie pop? Don’t overthink your questions. If it’s something that interests you, then go ahead and just ask.

This is a good way to start an engaging conversation and keep yourself (and your date) interested in talking more and getting to know one another. We happen to have already come up with a list of good online dating questions for guys and girls trying to keep the spark alive and find out if they’re a compatible match.

Whether you’re chatting in person or online, asking a personal or thought-provoking question keeps the dreaded awkward silence at bay and gives your date something to respond to. And who knows? You might just find their answers really fascinating.

3. Edit or Add to Your Dating Profile

You can give your dating profile a quick makeover to attract more attention online. It doesn’t have to be a complete overhaul — maybe just give it another look, and make sure it represents the best of who you are. Edit the wording, update the information, or maybe add another picture.

Editing a dating profile is a quick and effective way to give yourself a virtual face lift and draw more eyes to all you’ve got going on. Plus, a lot of dating sites and apps will highlight your profile to other members if they see you being active and taking steps to improve your online dating experience.

4. Go on a Photo Shoot Adventure

Your photos are often the most important aspect of your dating profile. The photos you choose make up your first impression, so you better make it a good one. Bustle reported that even though about 80% of profile pictures on Hinge are posed, the candid photos were actually more successful at attracting attention. On average, candid shots were 15% more likely to receive a like from a user on the quality-focused relationship app.

You can create a more engaging and attractive dating profile by grabbing an artsy friend of a professional photographer and taking high-quality pictures of yourself at a dog park, reading a book, playing a sport, or just going about your day.

A standout pic on your profile can generate more interest among potential online matches.

Online Profile Pros offers profile assessments and photo shoots for online daters in the US and Canada. They take professional-grade head shots and on-location pictures to make any dating profile shine. If you’re in the UK, you can make an appointment with Hey Saturday to go out with a photographer and come away with beautiful pictures.

5. Challenge Yourself to Say Yes & Take Risks

In the weeks after I saw Jim Carrey’s “Yes Man,” I decided I wanted to emulate that kind of positivist approach to life and say yes to opportunities for fun. By being optimistic and accepting all friendly invitations, I soon found myself at a party where I met and exchanged numbers with a very good-looking pre-med student.

The say-yes philosophy can help your online dating experience in a similar way. When you start swiping right on more people and responding to more initial messages (yeah, even the “sups”), you increase your odds of meeting someone who catches your eye.

Sometimes just being open to the possibility of romance is enough to bring romance into your life. Challenge yourself to say yes, within reason, on a dating site or app, and you’ll definitely have more interesting conversations, dates, and experiences.

6. Get a Friend to Pick Matches or Write Responses For You

One time my friend handed me his phone while he was on Tinder and asked me to swipe through girls for him. I eagerly took up the challenge. It was really interesting to see the interface from a guy’s perspective and to try to pick out a quality girl for my friend. My match selections helped him broaden his dating horizons and talk to someone he might’ve overlooked if he was swiping on his own.

If you’re up for it — and have a friend you trust with your love life — exchanging dating profiles for an afternoon could help you get you out of any online dating rut. It’s a fun experiment to try. Once you get a friend involved in the process with you, you might just find yourself enjoying the experience more because you know you’re not in it alone.

7. Plan Dates at Unusual or Entertaining Places

I know a guy who always takes his dates to the same restaurant. Week after week, he has a set first-date and second-date pattern that would really make me want to tear my hair out — but he seems to enjoy it. That life isn’t for everyone, though.

By escaping the dull dinner-movie routine, you and your online dates can have a lot of fun.

If your online dating routine is getting stale, I’d recommend mixing things up at a bowling alley, a bookstore, a botanical garden, or anywhere, really, that isn’t a run-of-the-mill coffee shop. A new and engaging setting can help you loosen up and make a strong connection based on mutual interests.

Next time you’re planning a date, invite your online love interest to join you at something you legitimately enjoy doing. That way, even if the date is a dud, you’ll still get a treat out of it.

Whether it’s sharing the best cheeseburger in town or challenging someone to a game of air hockey, going somewhere off the beaten path can really add a lot of excitement to your dating life.

8. Go Into Your Date With Realistic Expectations

Sometimes the rollercoaster of high hopes and dashed dreams can really get online daters down as they navigate virtually endless romantic possibilities that all seem to lead to inevitable disappointment. If you enter every date thinking “This could be ‘The One,'” you’re probably not going to enjoy the experience very much. You don’t want to skip ahead of the getting-to-know-someone part of dating because that’s an important step to falling for someone.

Make sure you’re being realistic about what you can expect with a night out with a complete stranger. First dates should be lighthearted introductions, not rigorous job interviews. Being a good listener, an engaging conversationalist, and pragmatic dater can help you avoid online dating burnout because you’re putting your focus and energy on enjoying the date at hand instead of looking ahead to a future that may or may not come to pass.

Keep Your Interest & You Might Just Interest an Attractive Date

I don’t know about you, but after a while of churning through hundreds of dating profiles and juggling dozens of superficial chats, I start to lose track of who’s who and what I even want from them. It’s easy to get burnt out with online dating — and that’s why it helps to give yourself goals, projects, and games to pass the time while you look for a hot date.

In my experience, the best way to keep your online dating experience interesting is to throw yourself into it and keep moving forward. Remember dating is supposed to be fun. Don’t take it too seriously. I don’t sweat it if I forget a name here or there because I know the important dates will make themselves memorable while everyone else just fades away.

Hopefully, our list of ideas can help you get interested in online dating again and meet someone who holds your interest — for at least a date or two.

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Amber Brooks

Amber Brooks is a Contributing Editor at DatingAdvice.com. When she was growing up, her family teased her for being "boy crazy," but she preferred to think of herself as a budding dating expert. As an English major in college, Amber honed her communication skills to write clearly, knowledgeably, and passionately about topics that interest her. Now with a background in writing, Amber brings her tireless wit and relatable experiences to DatingAdvice.com.

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